반응 #1483034

반응 방정식

tert-butyl 2-aminoethylcarbamate

Et3N

nicotinic acid

oxalyl chloride

→

tert-butyl 2-(nicotinamido)ethylcarbamate

수율 74.0%

용매

CH2Cl2

CH2Cl2

반응 조건

후처리

1. 1
   workup.DISSOLUTIONhad dissolved
2. 2
   기타(1 h)
3. 3
   기타The resulting reaction mixture
4. 4
   온도was warmed to room temperature
5. 5
   workup.STIRRINGstirred for 2 h
6. 6
   세척It was then washed with brine
7. 7
   건조dried over Na2SO4
8. 8
   여과filtered
9. 9
   농축concentrated under reduced pressure
10. 10
    기타Purification by silica gel chromatography (CH2Cl2)

실험 절차

In a typical run, nicotinic acid (2.0 g, 16.2 mmol) was taken up in CH2Cl2 (20 mL) along with oxalyl chloride (1.4 mL, 16.2 mmol). After a few drops of DMF were added, the reaction mixture was stirred at room temperature until all the solids had dissolved and all gas evolution had ceased (1 h). This freshly prepared solution of the acid chloride was added dropwise at 0° C. to a solution containing tert-butyl 2-aminoethylcarbamate (2.6 g, 16.2 mmol) and Et3N (3.4 mL, 24.2 mmol) in CH2Cl2 (200 mL). The resulting reaction mixture was warmed to room temperature and stirred for 2 h. It was then washed with brine, dried over Na2SO4, filtered and concentrated under reduced pressure. Purification by silica gel chromatography (CH2Cl2) afforded tert-butyl 2-(nicotinamido)ethylcarbamate (3.1 g, 74%).

출처